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To celebrate my daughter’s high school graduation (and also visit our 50th state … yep, we’ve been to them all now!) we went to Hawaii for a 7-day Hawaiian cruise on the Norwegian Pride of America! What an incredible and amazing trip. We wanted to spend as much time in The Aloha State so we flew out a few days early for a pre-cruise vacation …

Day 0 (Tuesday, May 28, Tampa)

We’ve got an early (all-day) flight tomorrow so after attending my daughter’s last high school banquet/awards ceremony, we drove to the Tampa airport, parked the car in the long-term parking garage, and checked into the Airport Marriott for the night.

Day 1 (Wednesday, May 29, Tampa – Oahu)

We got up early (although not as early as if we had had to drive from home), checked out of the hotel, and went downstairs to check in for our flight to Chicago and drop off our luggage. We’d been planning and saving for this vacation for literally years, and spared no expense. Flying first class on United to Chicago was a very pleasant experience. It got even better for our flight from O’Hare to Hawaii! The first class cabin on the Boeing 777-200 was amazing. My wife and daughter have flown internationally before, but even back in my road-warrior/frequent-flyer/travelling consultant days I had never had a big seat “pod” that reclined all the way flat into a bed. Very cool. That definitely helped the ~4,200mi, 8.5hr flight go by nicely. The only problem with our seats was the orientation. We should have picked the center section which was three across so we could all sit next to each other. Instead we had picked two rows on the windows side (two window seat, one aisle) which meant we had my wife and daughter sitting next to each other, but then the I was on the other side of the little wall containing the entertainment system. So to see them or talk to them, I had to stand up and look over that little dividing partition, which probably annoyed my seatmate a little.

We left Chicago at 10:30am and landed at Daniel K. Inouye International Airport in Honolulu at 2:30pm local time (8:30pm back at home). After collecting our suitcases we ordered an Uber that took us to our hotel, the Hilton Hawaiian Village. We had a pre-night hotel arrangement through Norwegian Cruise Line and just extended it a few days before for our pre-vacation vacation. After checking in we spent a little time unpacking and settling into our room in the Rainbow Tower which had an amazing view of Waikiki Beach. We had some time to walk around and acquaint ourselves with the resort before returning to our room to change and then headed for the Rooftop Starlight Luau.

The evening weather was beautiful. Sitting on the roof, sipping Mai Tais, eating from the buffet, and watching the Polynesian cultural show (fashion show, music, dancing, etc.) was a perfect way to spend our first night in Hawaii. We saw with a nice family from Orange County that was celebrating their 15th wedding anniversary and their daughter’s 8th grade graduation. Since we were also celebrating a graduation we had things to talk about. But afterwards, the travel and 6 hour time difference caught up with us and we crashed back in the hotel room (at least it wasn’t too far a walk).

Day 2 (Thursday, May 30, Oahu)

My wife and I woke up early (feeling like we’d adjusted to the time zone change) and took a walk down on the beach, letting my daughter sleep in a bit. After we showered, and dressed, we walked across the street and rented a little Mini Cooper convertible for the day.

Our first stop was for breakfast at Leonard’s Malasada Mobile Wagon for (what else?) hot, fresh, malasadas. My wife has a Portuguese background so having these in Hawaii was a must-do (there were some small ones at the luau buffet last night, but these are the real deal). After eating and licking the sugar from our fingers (I had a haupia (coconut filled) one), we drove to the North Shore, stopping at Sunset Beach. It wasn’t winter, so there weren’t a lot of surfers out, but the surf and waves were pretty big (based on our Florida standards). The beach itself was pretty empty, so we walked around for a bit taking scenic photos.

On the way back we stopped in Haleiwa Town to get some shave ice (another must-do on our list) at Matsumoto’s and checked out the little shops. I found a snack for the road, which turned out to be a family favorite: furikake potato chips! We continued driving back through the middle of the island on Kamehameha Highway and stopped next at the Dole Plantation. We did pretty much everything there: sampled fresh pineapple, rode the train and learned about the history of the pineapple industry on the island, and stumbled our way through the pineapple hedge maze.

We got stuck in rush hour traffic coming back through Honolulu. We wanted to go hiking but had forgotten to bring our change of shoes so we swung back past the hotel. My wife circled with the rental car while my daughter and I ran up to our room to retrieve our hiking shoes. Then we drove through more rush hour traffic out to the Lyon Arboretum and the hiked the Manoa Falls Trail. We were glad we stopped for the change of shoes! The trail is only 1.6 miles roundtrip, but was very wet and muddy. The scenery was amazing and while the “falls” at the end were really just a little trickle and not super-impressive, the surroundings more than made up for it.

With muddy shoes and a somewhat dirty convertible (you pick up a lot of sand and grit driving with the top down!) we drove back to Honolulu, returned the rental car, and walked back to the Hilton Hawaiian Village. After freshening up a bit, we walked down the street a ways to the Tropics Alehouse and had a nice dinner outside. What a great first full day in Hawaii!

Day 3 (Friday, May 31, Oahu)

This morning we started with malasadas for breakfast, of course. This time, though, we biked (using Biki) from the hotel to Leonard’s Bakery. The place (and the tiny parking lot) was packed, as we expected, so riding the bikes there was a good idea (plus, it helped justify having malasadas for breakfast again!). This time I tried the Li hing mui (spicy) one and really liked it! After breakfast we biked (Biki’ed?) back to the far end Waikiki Beach (near the Honolulu Zoo, you can watch a timelapse of our trip here) and walked along Kalakaua Avenue back to the Hilton Hawaiian Village.

Back in the hotel room, we started packing up, as tomorrow we board the cruise ship! We had one more must-do while we were on Oahu and that was Pearl Harbor. We had purchased our tickets in advance yesterday so once we were all ready, we headed outside and took an Uber out to the monument (we decided it wasn’t worth it to rent a car for today). What can I say? Pearl Harbor is a sobering place to visit … very powerful. Unfortunately the USS Arizona Memorial is closed for repairs, but we did take the boat ride out to Battleship Row which passed close by.

We took another Uber back to the hotel and grabbed some mid-afternoon ice cream at Lappert’s before heading back up the room to change. Time for some beach time! We wanted to try paddle boarding so we rented a board and alternated paddling (and swimming, and riding) in the salt water lagoon. It was actually a little easier than we thought (at least in the calm water of the lagoon) and we really enjoyed it! I think we’re going to try it more when we get back home to Florida.

It was now late afternoon/early evening so we went back to the room to clean up for dinner. While my wife and I were finishing up my daughter went to get a henna tattoo down in the village. We met up and then went over to the Goofy Cafe for dinner. My wife enjoyed her acai bowl but I found my (heads-on!) shrimp to be a little messy and not quite to my liking. Still, the atmosphere was nice even though we were downstairs at the one community table near the kitchen instead of upstairs in the main dining room.

After dinner we walked back to the beach for the Friday night fireworks at the Hawaiian Village. We had hoped to be able to see them from our hotel balcony, but after doing a little online research and dinner it appeared that they would be shot off from a part of the beach out of our view. So we stayed down on the beach (with just about everyone else staying at the resort) for the short, but beautiful, fireworks display.

Trying to get off the beach after the fireworks reminded us of trying to leave a Disney park after the fireworks … jam packed! We ended up walking around the little shops a bit more and listening to an 80s cover band that was rocking out in one of the open bars of the village. Finally back in the hotel room, we finished re-packing the suitcases for the cruise tomorrow. Then the real vacation begins!